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Ammonia → HCID 178484230, Verbindung

HRID 1917181
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1917181
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][N:13]([CH3:22])[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][CH2:8][S:7][C:6]=2[CH:23]=1.I.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](SC)=[NH:31].N>CCO.C(Cl)Cl.CO>[CH3:22][N:13]([CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][S:7][C:6]2[CH:23]=[C:2]([NH:1][C:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)=[NH:31])[CH:3]=[CH:4][C:5]1=2)[CH2:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16]
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Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 59144141tert-Butyl 2-((2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)(methyl)amino)acetateHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 178484230HCID 178484230, VerbindungAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel
HCID 887MethanolLösungsmittel2×
HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of tert-butyl 2-((2-(7-amino-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)(methyl)amino)acetate (850 mg, 2.52 mmol) in EtOH (25 mL) was added methyl thiophene-2-carbimidothioate hydroiodide (1.43 g, 5.04 mmol). The resulting suspension was stirred at room temperature for 17 hours (overnight). At this time, the suspension was diluted with 20 mL CH2Cl2 to give a dark yellow solution. Argon was then bubbled through this solution for 30 minutes. The solution was transferred to a separatory funnel containing saturated sodium bicarbonate solution (50 mL) and CH2Cl2 (100 mL) then extracted. After extraction, the organic layer was separated, dried (Na2SO4), filtered, and concentrated to give a dark residue. This residue was subjected to flash chromatography on silica gel using 2:98 MeOH:CH2Cl2 followed by 2.5:97.5 (2M NH3 in MeOH):CH2Cl2 to give a yellow-green residue (420 mg, 37.3%). Some impure fractions were collected (˜340 mg). 1H-NMR (CDCl3) δ 7.43-7.35 (m, 2H), 7.06 (pseudo t, J=4.8 Hz, 1H), 7.71 (brd, J=8.1 Hz, 2H), 6.65 (dd, J=1.8, 8.4 Hz, 1H), 4.91 (brs, 2H), 3.66-3.58 (m, 2H), 3.43 (t, J=7.2 Hz, 2H), 3.21 (s, 2H), 3.07-2.99 (m, 2H), 2.74 (t, J=7.5 Hz, 2H), 2.45 (s, 3H), 1.47 (s, 9H); ESI-MS (m/z, %): 447 (MH+, 100), 391 (50); HPLC purity: 99.7% a/a.

Aufarbeitung

  1. customto give a dark yellow solution
  2. customArgon was then bubbled through this solution for 30 minutes
  3. customThe solution was transferred to a separatory funnel
  4. additioncontaining saturated sodium bicarbonate solution (50 mL) and CH2Cl2 (100 mL)
  5. extractionthen extracted
  6. extractionAfter extraction
  7. customthe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a dark residue

Quellen und Nachweise

ORD-Eintrag
ord-d304bdbde1104b1c846deeb1626a38c7
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08618286B2

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